Hydrochloric Acid → 3-Carbamoyl-5-dipropylcarbamoyl-benzoic acid

HRID 1350924Notes

Reaction equation

HRID 1350924 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:13]=1)[C:7]([O:9]C)=[O:8])=[O:3].[OH-].[Na+].Cl.O>CO>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:13]=1)[C:7]([OH:9])=[O:8])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22593626Methyl 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoate

Product 1

HCID 223948913-Carbamoyl-5-dipropylcarbamoyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoate (XXII, PREPARATION 5, 0.197 g, 0.64 mmol) in methanol (5.0 mL) is added sodium hydroxide (1N, 3.0 mL). The mixture is stirred at 20–25 degrees C. for 24 hours. The mixture is acidified to about pH 5 with hydrochloric acid (10%). Water (50 mL) is added and the mixture is washed twice with ethyl acetate (2×50 mL). The organic extracts are combined and dried over anhydrous magnesium sulfate and concentrated to give the title compound, NMR (DMSO-d6) delta 0.66, 0.930, 1.48, 1.62, 3.12, 3.35, 7.54, 7.98, 8.22 and 8.51.

Workup

  1. washthe mixture is washed twice with ethyl acetate (2×50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0925424cc7a4476ab94f6f4c83a35651
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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